Deer Santa Festival

Picture Pittsfield is proud to host the 3rd Annual Deer Santa Festival on Sunday. Nov. 28, 2021.

The live events: the Santa Parade, Christmas Tree Lighting ceremony, Holiday Market and live reindeer visit, all scheduled for the afternoon of Nov. 28. 

However, rather than focus how we CAN’T celebrate, let’s talk about what we CAN do to celebrate:

Deer Santa Yard Deer Display Challenge – We had 47 deer on display last year… we’re hoping to grow the herd even bigger this year! You can purchase a blank wooden yard deer through Picture Pittsfield for $40 ($30 cost, $5 donation to the Pittsfield High School wood shop for cutting out the deer for us and $5 donation towards the Deer Santa Festival expenses). Pickup from Pikeland Motors. 118 N. Monroe St., Monday through Friday, 9 a.m.-5 p.m. Deer will be sold on a first-come, first served basis, no holds or pre-orders. Due to fewer school days because of COVID, fewer deer will be available this year, so plan to purchase yours early. When you pick up your blank deer, please pay the $40 cost by cash or check made out to Picture Pittsfield only – no credit or debit cards.

If you have a deer from last year, you can enter it as is, or redecorate it. To enter your previous year’s deer in the display, it will be a $10 donation, cash or check made out to Picture Pittsfield. These donations will go toward Deer Santa Festival expenses and materials. The $10 is payable at deer display drop off on Nov. 28. There’ll be a box available for a touch-less exchange.

Decorate your deer any way you like (family friendly, please!), give it a name, and then deliver it back to the Pittsfield courthouse square between noon and 3 p.m. Nov. 28 so that Picture Pittsfield volunteers can add it to the display.  Be sure to give it to a Picture Pittsfield volunteer so the proper info can be recorded for your entry in to the contest. Top deer will win fun prizes! Deer need to be removed from the courthouse lawn by their owners between Saturday, Jan. 2 and Wednesday, Jan. 6, 2021.

Some of the 2019 Deer Santa Display Challenge entries.

Christmas Wreath Auction at Courtyard Cafe and Bakery

Businesses and individuals are invited to “adopt” an undecorated wreath from Courtyard Cafe and Bakery for $10, decorate it, and then return it for display. Wreaths will be sold on a first-come, first served basis. Photos of the wreaths will also be placed on Facebook for virtual viewing. Details about that will come out soon. A silent auction for each wreath will begin Dec. 1 and continue through 5 p.m. Thursday, Dec. 10. At that time, the silent auction will close and wreath winners notified. Proceeds benefit Picture Pittsfield’s 2021 local community projects.

Help Decorate the Community Christmas Tree

Take an ornament home and decorate it for the community tree! Starting Nov. 11, you can pick up a free blank ornament for each child in your family to decorate. Ornaments will be available at these Pittsfield locations: The Pike County Chamber of Commerce Office (in the 24 hour foyer separating the Chamber from the Community Center), 224 W. Washington St., Pittsfield City Hall, 215 N. Monroe St., County Market, 825 W. Washington St., and William Watson Cafe, 107 E. Washington St., and Walmart on Shetland Drive. Decorate it any way you like – tips will be posted to the Picture Pittsfield Facebook page in the coming weeks. Add your name, if you like, and then bring your decorated ornaments to the Courthouse Lawn Nov. 29 and hang it wherever you like on the community Christmas Tree. It’s the evergreen tree on the west side of the square, across the path from Santa’s House. Questions can be emailed to

Letters to Santa

Between Sunday Nov. 29-Friday, Dec. 18, children can “mail” their letters to Santa by dropping them off at Santa’s House on the Courthouse Lawn. Any letter with a mailing address will be answered! A big thank you to the city’s front office staff for making this possible!

Letters to Santa can be “mailed” at Santa’s House on the Pike County Courthouse Lawn.

“Light It Up Pittsfield” Holiday Decoration Contest – Dec. 18, 2020, 5:30-8:30 p.m.

Here’s your chance to officially become the Clark Griswold of Pittsfield! Picture Pittsfield volunteers will be touring the city between 5:30-8:30 pm Friday, Dec. 18 and selecting two outdoor holiday decor winners: Business and Residential. Business are office buildings, shops and restaurants. And residential entries are decorated homes, any size and shape. Residences and businesses must be within the Pittsfield city limits. A winner and runner up will be selected in each category for a total of four winners. Entries will be judged on creativity and overall attractiveness.

Categories:  Residential (houses, duplexes, apartments) and Business (window or store front /locally and commercially owned).   Each category can win 1st Place and Runner Up.

The things judges will be looking for:

Lights – We are looking for brightness, colors, organization and movement.

Theme – We will be looking for Christmas themes. Think movies, songs, stories,  etc. 

Spirit – We are looking for the house or business that encompasses what Christmas is all about.  

Residential and businesses will be judged on a scale of 1-5 

5.  Beyond Exceptional

4.  Exceptional

3.  Middle of the Road

2.  Best Attempt

1.  Minimalist

Be sure to have all lights and animation on between the hours of 5:30-8:30 pm Friday, Dec. 18. If you would like your business or residence to be judged then please send your name, address, email and phone number to: by Sunday, Dec. 13, 2020.

The Deer Santa Festival was launched in 2019 as a project of the community organization, Picture Pittsfield. Area businesses and organizations host holiday activities around the community and are listed on one community calendar. The festival kicks off with a Santa Parade and Christmas Tree Lighting event the Sunday after Thanksgiving and activities continue through December.